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Caribbean Islands

$110+ Cheap flights from Madison (MSN) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheap flight deals from Madison to Caribbean Islands

Cheapest flights from Madison to Caribbean Islands
Explore the most affordable flight options available from Madison to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.

This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2410:58 am
MSN
-
SJU
1 stop7h 41m
American Airlines
Wed 3/45:42 pm
SJU
-
MSN
1 stop18h 26m
American Airlines
Deal found 2/3$256
This Priceline deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:50 pm
MSN
-
SJU
1 stop13h 37m
Frontier
Sun 3/83:19 pm
SJU
-
MSN
1 stop21h 15m
Frontier
Deal found 2/1$270
This Priceline deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:50 pm
MSN
-
SJU
1 stop13h 37m
Frontier
Sat 3/149:41 pm
SJU
-
MSN
1 stop14h 48m
Frontier
Deal found 2/1$313
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:30 am
MSN
-
SJU
1 stop7h 10m
United Airlines
Tue 3/101:05 am
SJU
-
MSN
2 stops14h 53m
United Airlines
Deal found 2/1$316
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/149:41 am
MSN
-
SJU
2 stops12h 31m
Delta
Tue 4/216:15 am
SJU
-
MSN
2 stops12h 21m
Delta
Deal found 2/1$332
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/187:15 am
MSN
-
SJU
1 stop11h 24m
American Airlines
Tue 3/101:30 am
SJU
-
MSN
1 stop10h 09m
American Airlines
Deal found 2/2$338
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:55 pm
MSN
-
SJU
1 stop11h 52m
Multiple Airlines
Thu 5/146:30 am
SJU
-
MSN
2 stops26h 55m
Multiple Airlines
Deal found 2/3$343
This American Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/68:24 pm
MSN
-
SJU
1 stop7h 00m
American Airlines
Fri 4/1011:59 pm
SJU
-
MSN
1 stop12h 06m
American Airlines
Deal found 2/1$359
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:45 am
MSN
-
SJU
2 stops12h 53m
United Airlines
Tue 10/61:05 am
SJU
-
MSN
2 stops9h 48m
United Airlines
Deal found 1/31$363
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:22 pm
MSN
-
GCM
2 stops15h 51m
American Airlines
Tue 3/102:35 pm
GCM
-
MSN
2 stops18h 33m
American Airlines
Deal found 2/3$364
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:51 am
MSN
-
SJU
1 stop8h 15m
Delta
Sat 5/237:00 am
SJU
-
MSN
2 stops11h 32m
Delta
Deal found 2/1$371
This Priceline deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/225:47 pm
MSN
-
SJU
1 stop7h 26m
Frontier
Wed 3/253:08 am
SJU
-
MSN
1 stop11h 13m
Frontier
Deal found 2/2$373

Find flight deals from Madison to Caribbean Islands

Keep the following information in mind while searching for Madison to Caribbean Islands flight deals. Data was last updated February 3, 2026.

Round-trip from

$251
(American Airlines)

One-way from

$110
(Priceline)

Popular in

March

Cheapest in

September

Average price

$482
From Madison Truax Field to Caribbean Islands
Search Deals
One-way flight from Madison Truax Field to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 3, 2026.
Use the filters below to find and compare flights from Madison to Caribbean Islands that are best for you.

Fly from

Madison

Fly to

Caribbean Islands

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 2/25

11:20 am-11:58 pm

1 stop10h 38m

San Juan Luis Munoz Marin Intl

Wed 3/4

4:30 pm-10:48 pm

1 stop8h 18m

$256

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 2/24

6:00 am-4:28 pm

1 stop8h 28m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:42 pm-10:08 am

1 stop18h 26m

$256

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 5/3

6:00 am-8:24 pm

2 stops13h 24m

San Juan Luis Munoz Marin Intl

Sat 5/9

7:00 am-5:32 pm

2 stops11h 32m

$256

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 3/3

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Wed 3/11

7:30 am-2:58 pm

1 stop8h 28m

$316

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 4/14

9:41 am-11:12 pm

2 stops12h 31m

San Juan Luis Munoz Marin Intl

Tue 4/21

6:15 am-5:36 pm

2 stops12h 21m

$332

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 4/6

8:24 pm-4:24 am

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Fri 4/10

11:59 pm-11:05 am

1 stop12h 06m

$359

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 3/7

8:22 pm-1:44 pm

1 stop16h 22m

George Town Owen Roberts Intl

Tue 3/10

7:45 am-9:39 pm

2 stops13h 54m

$364

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 5/16

10:51 am-8:06 pm

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Sat 5/23

7:00 am-5:32 pm

2 stops11h 32m

$371

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 3/4

11:20 am-9:12 pm

1 stop7h 52m

San Juan Luis Munoz Marin Intl

Tue 3/10

6:15 am-5:24 pm

2 stops12h 09m

$381

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 4/6

8:24 pm-4:24 am

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Thu 4/9

11:59 pm-11:05 am

1 stop12h 06m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 60 results
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Best time to book a flight from Madison to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Madison to Caribbean Islands

What is the cheapest month to book a flight from Madison to Caribbean Islands?

Currently, November is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $113). Flying from Madison to Caribbean Islands in June is currently the most expensive (average of $378). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated February 3, 2026.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Madison to Caribbean Islands. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,138 reviews

Food

7.2

Overall

7.9

Crew

8.5

Entertainment

7.8

Comfort

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,138 reviews
Delta
7.9
Good
8,138 reviews

Food

7.2

Overall

7.9

Crew

8.5

Entertainment

7.8

Comfort

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,236 reviews
Delta
7.9
Good
8,138 reviews

Food

7.2

Overall

7.9

Crew

8.5

Entertainment

7.8

Comfort

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,217 reviews
Delta
7.9
Good
8,138 reviews

Food

7.2

Overall

7.9

Crew

8.5

Entertainment

7.8

Comfort

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Madison to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Caribbean Islands?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Caribbean Islands. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • How long is the flight from Madison to Caribbean Islands?

    A quick flight from Madison to Caribbean Islands can take about 7h 10m. Delta provides one of the quickest options available for as low as $316. There are 2180 mi between Madison and Caribbean Islands. This flight may include one or multiple stops.

  • What are the most popular routes from Madison to Caribbean Islands?

    While some choose either Madison Truax Field - Punta Cana or Madison Truax Field - Oranjestad Reina Beatrix, Madison Truax Field - San Juan Luis Munoz Marin Intl is the most popular route from Madison to Caribbean Islands.

  • Can I find deals for flights from Madison to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Madison to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Caribbean Islands.

  • Can I find deals for business class flights from Madison to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Madison to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to Caribbean Islands?

    Currently, November is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $113). Flying from Madison to Caribbean Islands in June is currently the most expensive (average of $378). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Madison to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Madison to Caribbean Islands

Discover the top 3 airlines that operate flights from Madison to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$214Average$753FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$257Average$613FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$666FlexibilityNo cancel feeOn-time71%

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